Vat dyestuff of the antraquinone series and process of making same.



UNITED STATES PATENT OFFICE.

MAX HESSENLAND, F HGCHST-ON-THE-MAIN, GERMANY," ASSIGNOR T0 FARBWERKEVORM. MEISTER LUCIUS & BRIINING, 0F HGCHST-ONeTHE-MAIN, GERMANY, A COR-PORATION 0F GERMANY.

VAT DYESTUFF OF THE ANTRAQUINONE SERIES AND PROCESS OF MAKING SAME.

No Drawing.

To all whom it may concern.

Be it known that I, MAX HnssENLAND, Ph. D., chemist, a citizen of theEmpire of Germany, residing? at Hochst-on-the-Main, Germany, haveinvented certain new and useful Improvements in New Vat Dyestuil's ofthe Anthraqui'none Series and Processes of Making Same, of which thefollowing is a specification.

I have found that valuable vat dyestuffs can be-obtained byintroducinginto the amino group of the 4-amin0-anthraquinone-a-acridones, radicals,such as an alkyl-, arylor acidyl group, or an anthraquinone residue.Thus new dyest-ufls are produced the relation of which to the blue 4amino anthraquinone a. acridone (described in U. S. application Sr. No.589,997 filed Oct. 31, 1910) is apparent from the following formulae:

In the .latter formula C, stands'for a benzene residue and Rfor'instance for a y methyl, naphthyl, bromophenyl, benzoyl orSpecification of Letters Patent.

Application filed October 31, 1910. Serial No. 589,998.

Patented Sept. 5, 1911.

The process for obtaining the new dyestuffs consists in causing halogencompounds of the above-mentioned radicals to react with the said4-aminoanthraquinone-aacridones. 7

Example: There isboiled for hoursua mixture consisting of 10 parts oflt-amino- 1.2- anthraquinone acridone, obtainable from la-mino-1-anthraquinonyl-anthranilic acid for instance by the action ofchlorosulfonic acid,-l0 parts of a-chloroanthraquinone, one part ofcuprous chlorid, 5 parts of anhydrous sodium acetate and 400 parts ofnitrobenzene. The nitrobenzene is then removed by distillation withsteam and the remaining product forms a black powder, which is insolublein Water, alcohol, ether, alkalis and diluted mineral acids, butdissolves in concentrated'sulfuric acid to an olive-green solution. Inalkaline hydrosulfite it dissolves to a reddish-brownsolution and dyescotton gray to deep-black tints of excellent fastness. In an analogousmanner other organic radicals are introduced into the amino groupquinone-aoridone.

The following tabular statement shows the properties of some of thedyestuffs ob-,

of the 4=-amino-1.2-anthratainable by the new process:

anthraquinonyl.

Color of the Solution in concen- Color of the Dyeings on cm'lsmutionSubstance. trated sulfuric acid. vat. Cotton.

nn f I I L +a-chloroanthrequinone... Black Olive-green.Reddlsh-brown.... Graytoblack.

i +B-chloroanthraquinone..; Dark-green Grayish-green.

+benzoylchlor id Blue Reddish-b rownulu Violet Reddish-blue.

-|-bro1.uobenzene Dark-green Brown Green.

+p dibromobenzeno... Grayish-brown...... Green.

" +a-chloronaphthalene.... Blue Reddish-bi'own.... Bluish-gmy.

" +B-ch1oronaphthalene.... Dark-green Brown Violet Yellowish-green.

Having now described my what I claim is:

1. As products, new vat-dyestufi's, namely invention, the4-aminoanthraquinone-a-acridones containing an organic radical linked inthe amino group,- said dyestuffs being dark.

. .s powders, insoluble in water, alcohol, ether, alkalis and dilutedmineral acids, dissolving in concentrated sulfuric acid with a green tobrown color, in alkaline hydrosulfite with a violet to brown color anddyeing from these solutions cotton dark tints of quinon I linked in theamino group, said dyestu being a black powder, insoluble in water,alcohol, ether, alkalis, and diluted -mineral acids, dissolving inconcentrated sulfuricacid with an olive-green color, in alkalinehydrosulfite with a reddish-brown color and dyeing from this solutioncotton -anthraquinone-a-acridone with a halogen compound of an-organicradical. v

, In testimony whereof, I aflix my signature in presence of twowitnesses.

MAX HESSENLAND.

Witnesses:

CARL GRUND, JEAN GRUND.

